Potassium Phosphate, Tribasic → HCID 66653634, compound

HRID 409560Notes

Reaction equation

HRID 409560 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7](B(O)O)[CH:8]=[CH:9][CH:10]=1)=[O:4].P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:23]1[N:24]=[C:25]([C:32]([C:34]2[CH:35]=[C:36]3[C:41](=[CH:42][CH:43]=2)[N:40]([CH2:44][CH2:45][CH3:46])[C:39](=[O:47])[N:38]([CH2:48][CH2:49][O:50][C:51]2[CH:56]=[CH:55][C:54]([F:57])=[CH:53][CH:52]=2)[C:37]3=[O:58])=[O:33])[N:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=12>O.CN1C(=O)CCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:57][C:54]1[CH:53]=[CH:52][C:51]([O:50][CH2:49][CH2:48][N:38]2[C:37](=[O:58])[C:36]3[C:41](=[CH:42][CH:43]=[C:34]([C:32]([C:25]4[N:26]5[CH:31]=[CH:30][CH:29]=[CH:28][C:27]5=[C:23]([C:7]5[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=5)[C:3]([O:2][CH3:1])=[O:4])[N:24]=4)=[O:33])[CH:35]=3)[N:40]([CH2:44][CH2:45][CH3:46])[C:39]2=[O:47])=[CH:56][CH:55]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 66653446HCID 66653446, compound

Product 1

HCID 66653634HCID 66653634, compoundYield 69.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

2.178 g (12.1 mmol) of 3-methoxycarbonylphenylboronic acid, 4.279 g (20.16 mmol) of potassium phosphate dissolved in 30 ml of water, and 582.4 g (0.504 mmol) of tetrakis(triphenylphosphine)palladium are added to 5.7 g (10.08 mmol) of 6-[(1-bromoimidazo[1,5-a]pyridin-3-yl)carbonyl]-3-[2-(4-fluorophenoxy)ethyl]-1-propylquinazoline-2,4(1H,3H)-dione in 180 ml of NMP. The reaction medium is microwave-heated for 15 minutes at 120° C. and then concentrated under reduced pressure. The solid obtained is purified by silica gel column chromatography, elution being carried out with a dichloromethane/methanol (100/1) mixture. 4.32 g of a yellow solid are obtained.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe solid obtained
  3. customis purified by silica gel column chromatography, elution

Sources & evidence

ORD record
ord-f0ca694bbd3b4813b1a1c9d1236538ef
Source dataset
uspto-grants-2014_06
Patent number
US08759344B2

Reaction notes

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